Sailing

Experience Wed & Sat Chicago Fireworks Aboard Tall Ship Windy from Navy Pier

A Truly Special Event Sail! During the summer, every Wed & Saturday night, Tall Ship Windy sails from Navy Pier for our guests to enjoy the spectacular night fireworks from the best seat in town. Enjoy the amenities of the 148 foot, four masted Schooner that is the official ship of the City of ...

Chicago Skyline Tall Ship Sightseeing Cruise

Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. Windy is the Official Ship for the City of Chicago. At 148 feet long, she is one of only a ...

Chicago Private Sunset Sail on Lake Michigan

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline.  Make the experience your own.  The flexibility of a private ...

Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter ...

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline.  Make the experience your own.  The flexibility of a private ...

Educational Tour and Sail Aboard Chicago's Official Flagship Windy 148' Schooner

The educational sail aboard Chicago's Official Flagship Windy departs at 11am Thursday thru Monday from Navy Pier. Leave the hustle and bustle behind, and enjoy a leisurely Educational Sail aboard Chicago’s Official Tall Ship. Guests will enjoy 75 minute sail where they will learn about sailing ...

Monday Night Blues Summer Concert Series Aboard Tall Ship Windy

Join us for a 2-hour concert sail from 7pm-9pm every Monday this Summer! Chase your Monday BLUES away aboard the 148 foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied by the sweet sounds of the blues. Whether you’re a long-time fan or ...

Chicago’s Famous Friday Night Pirates Pub Sail Aboard 148' Tall Ship Windy

Take in the world-famous skyline of the Windy City from the water, and enjoy a leisurely trip on Lake Michigan aboard Chicago's Famous Pirates Pub.Your ticket includes one complimentary rum punch, domestic beer, soda or water, per person. Duration: 2 HoursChicago’s famous Pirates Pub Sail ...

Private Evening Sail in Chicago Ending with Navy Pier Fireworks

Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. Over the course of two hours, you’ll sail along Chicago’s beautiful lakefront with a view of the city skyline. You’ll have the perfect vantage point to enjoy the incredible ...